Diindenopyrazines: Electron-Deficient Arenes.

We report the syntheses, properties and application of air stable, electron acceptors, the diindenopyrazines 4a-g . We demonstrate introduction of functional aryl groups in 6,12-position. The targets are accessible on the hundred milligrams to the gram scale. The structure of the aryl groups in 4a-g modulate the solubility, redox potentials and optical properties. Introduction of electron poor aryl groups to the electron poor diindenopyrazine backbone reduces the electron affinity to -4 eV, attractive as n-semiconductors. A simple organic field-effect transistor - without optimization - of 4e shows electron transport with a mobility of up to 0.037 cm 2 /Vs.